-23- ORGANIC CHEMISTRY
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1 -23- RGANIC CEMISTRY A. STRUCTURE AND ISMERISM 1. Structure (a) number of bonds to C,,, N and halogen (b) chain formation via C C bonds (c) straight and branched chains - isomerism (d) general formulae for alkanes, cycloalkanes, alkenes and alkynes - units of unsaturation (double-bond equivalents) 2. Structural isomerism (a) chain isomerism (b) positional isomerism (c) functional group isomerism 3. Geometric (cis-trans) isomerism (a) in cycloalkanes (b) in alkenes 4. ptical isomerism in compounds with an asymmetric (chiral) carbon atom B. FUNCTINAL GRUPS AND IUPAC NMENCLATURE (see also the NAMING program in the Chemistry Lab) 1. Alkanes and Cycloalkanes 2. Alkenes and Cycloalkenes 3. Alkynes 4. Aromatic compounds (a) monosubstituted (including toluene, phenol, aniline, benzaldehyde & benzoic acid (b) disubstituted (1,2-, 1,3, 1,4 and o-, m-, p-) (c) polysubstituted (1,2,4-, etc.) 5. alogen derivatives 6. Alcohols (a) monohydric (one ), dihydric (diols; two ), trihydric (triols; three ). (b) primary (1 ), secondary (2 ), tertiary (3 ). 7. Ethers (acyclic only) as dialkyl ethers, alkyl alkyl ethers and alkoxy alkanes 8. Aldehydes 9. Ketones 10. Carboxylic acids and derivatives (salts, esters, anhydrides & amides) (a) monoacids, diacids, etc. (b) esters 11. Amines (a) as alkyl amines and alkanamines (b) primary (1 ), secondary (2 ) and tertiary (3 ) C. RGANIC REACTINS (Reaction type in italics; see Section D) 1. Alkanes (a) combustion (oxidation) - 2 /heat (b) halogenation (substitution) - 2 or 2 /light or heat
2 Alkenes (a) hydrogenation (addition) - 2 /Pd (b) halogenation (addition) - 2 or 2 (c) hydrohalogenation (addition) - or (d) hydration (addition) - 2 / (e) hydroxylation (oxidation) - cold dil. alkaline KMn 4 (f) oxidation to ketones and acids (oxidation) - hot conc. KMn 4 3. Alkynes (a) hydrogenation (addition) - 2 /Pd (b) halogenation (addition) - 2 or 2 (c) hydrohalogenation (addition) - or 4. Aromatic compounds (a) halogenation (substitution)- 2 or 2 /Fe (b) conversion of alkyl substitutents to C (oxidation) - hot KMn 4 5. Alcohols (a) reaction with alkali metals (reduction) - Na, Li or K (b) dehydration (elimination) - conc. 2 S 4 (c) 1 to aldehydes & acids (oxidation) - KMn 4 (d) 2 to ketones (oxidation) - KMn 4 (e) ester formation (substitution) - acids or anhydrides/ 6. Aldehydes (a) conversion to acids (oxidation) - KMn 4 (b) conversion to 1 alcohols (reduction or addition) - 2 /Pd 7. Ketones conversion to 2 alcohols (reduction or addition) - 2 /Pd 8. Carboxylic acids (a) reaction with base (acid-base) - NaC 3 or Na (b) ester formation (substitution) - alcohol/ (c) amide formation (substitution) - amine or ammonia 9. Esters hydrolysis (substitution) - 2 and or Amides hydrolysis (substitution) - 2 and or Amines (a) reaction with acid (acid-base) - e.g., C 3 C, etc. (b) amide formation (substitution) - carboxylic acids/heat 12. Phenols (a) reaction with strong base (acid-base) - Na (b) ester formation (substitution) - anhydrides/ D. TYPES F RGANIC REACTINS 1. Addition Reaction in which a reagent is added to the double (or triple) bond between two carbon atoms or the double bond between a carbon atom and an oxygen atom.
3 -25- (a) hydrogenation ( 2 /Pd) i) alkene or alkyne to the corresponding alkane 2 (excess) Pd ii) aldehyde or ketone to the corresponding alcohol Pd 2 (excess) (b) halogenation ( 2 or 2 ) alkene or alkyne to the corresponding alkyl dihalide or tetrahalide 2 2 (excess) (c) hydrohalogenation ( or ) i) alkene to the corresponding alkyl halide (Markovnikov) ii) alkyne to the corresponding alkyl dihalide (Markovnikov) (excess) (d) hydration ( 2 / ) alkene to the corresponding alcohol (Markovnikov) 2
4 Elimination Removal of a small molecule from a compound to produce a double or triple bond. dehydration ( 2 S 4 ) alcohol plus concentrated acid to the corresponding alkene concentrated 2 S 4 3. Substitution Exchange of an atom (or group of atoms) for another (a) halogenation ( 2 or 2 ) (i) alkane to the corresponding alkyl halide 2 heat or light (ii) benzene (with Fe catalyst) to the corresponding aryl halide Fe 2 (b) esterification/amide formation (i) alcohol plus carboxylic acid to the corresponding ester C 3 C 2 C 2 2 (ii) amine plus carboxylic acid to the corresponding amide C 3 N 2 heat N 2 (c) ester/amide hydrolysis (i) ester plus aqueous acid (or base) to the corresponding alcohol plus carboxylic acid 2 (C 3 ) 2 C-
5 -27- (ii) amide plus aqueous acid (or base) to the corresponding amine plus carboxylic acid N K N 2 - K 4. Acid/Base Transfer of ion from an acidic compound to a basic compound neutralization (i) carboxylic acid plus a base to the corresponding salt - Na NaC 3 2 C 2 (ii) phenol plus a strong base to the corresponding salt - Na - Na 2 (iii) amine plus an acid to the corresponding salt C 3 C 2 N 2 C 3 C 2 N 3-5. xidation-reduction 1. xidation Reaction with an oxidizing agent to produce a compound which, in many cases, contains a carbon oxygen double bond (a) oxidation of alcohols (i) primary alcohol to the corresponding aldehyde (mild conditions) or the corresponding carboxylic acid (hot) KMn 4 KMn 4
6 -28- (ii) secondary alcohol to the corresponding ketone KMn 4 (b) oxidation of alkenes (i) alkene to the corresponding diol KMn 4 (cold) (ii) alkene to the corresponding carboxylic acid or ketone KMn 4 (hot) KMn 4 (hot) (c) oxidation of alkylbenzenes alkyl benzene to the corresponding benzoic acid KMn 4 (hot) C 2 2. Reduction (a) reduction of aldehydes and ketones to alcohols see 1 (a) (ii) (hydrogenation of aldehyde or ketone) (b) active metal plus alcohol to the corresponding salt - Na Na 2
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